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Chatham Rentals

From $756 per night (USD)
VRBO
Excellent Chatham Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This Chatham beauty is a Newly built cottage which is walking distance to Pleasant Bay and a short drive to town. A per ...
From $756 per night (USD)
VRBO
From $1051 per night (USD)
VRBO
Family friendly luxury home with heated pool and spa
Bedrooms:
5
Bathrooms:
4
Sleeps:
14
Gorgeous home in Chatham with a brand new heated saltwater pool and hot tub. The open floor plan, combined living and ...
From $1051 per night (USD)
VRBO
From $365 per night (USD)
VRBO
Cozy one bedroom on White pond (Must bring your own linens)
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
2 Person only. Charming little classic Cape cottage located close to town, beaches and bike trail. The cottage is nestl ...
From $365 per night (USD)
VRBO
From $403 per night (USD)
VRBO
Quaint 2 Bedroom Cottage Overlooking White Pond
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Must bring your own linens. Perfect getaway to relax and unwind. Located in a small 5 acre enclave of cottages nestled u ...
From $403 per night (USD)
VRBO
From $1578 per night (USD)
VRBO
Location! Pool & Spa! 2 Primary Suites, Walk to Town, Beach, Chatham Bars Inn
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
**Please enter desired dates for accurate pricing.*** LOCATION: Your perfect Chatham vacation starts here in this newly ...
From $1578 per night (USD)
VRBO
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VRBO
Large Yard, Quiet; 300 Yd on Sidewalk to Hardings Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
If you have small children or would just like some peace and serenity, Blue Skye is for you. Lots of lawn to run and pl ...
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VRBO
From $502 per night (USD)
VRBO
Pleasant Chatham Cape
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Pleasant Chatham Cape - A Classic Cape Cod Getaway with Modern Comforts Welcome to Pleasant Chatham Cape, a charming 4- ...
From $502 per night (USD)
VRBO
From $687 per night (USD)
Expedia
Solitude near the beach, High speed wifi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Comfort, convenience and beauty a mere 5 minute stroll away from Ridgevale beach. Nestled in a quiet neighborhood, our b ...
From $687 per night (USD)
Expedia
From $1050 per night (USD)
VRBO
Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
A charming 3 bedroom, 2.5 bath cape with large kitchen and private backyard, patio and deck that abuts conservation lan ...
From $1050 per night (USD)
VRBO
From $571 per night (USD)
Expedia
Centrally located home with patio, a/c included, walking distance from town.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Centrally located vacation home with central air conditioning in an ideal location with 3 bedrooms, 2 full baths plus ...
From $571 per night (USD)
Expedia
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VRBO
FIVE BEDROOM -- AMAZING WATER VIEWS OF NANTUCKET SOUND, MINUTES TO ASSOCIATION BEACH
Bedrooms:
4
Bathrooms:
5
Sleeps:
11
Just 1/10 of a Mile to Deeded Association Beach with amazing water views of Nantucket Sound. * * * * See end of ...
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VRBO
From $1085 per night (USD)
VRBO
Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
1.2 acres of beautiful waterfront property. Pond is great for canoes, fishing, and swimming. Canoe provided for tenant u ...
From $1085 per night (USD)
VRBO
From $366 per night (USD)
VRBO
Renovated cottage 1 mile to beach in Chatham!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Totally renovated bungalow style cottage with a sunny open floor plan, brand new appliances and furnishings on quiet str ...
From $366 per night (USD)
VRBO
From $906 per night (USD)
VRBO
FOUR BEDROOM IN TOWN LOCATION -- CLOSE TO OYSTER POND BEACH AREA.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Wonderful In Town Location with a Main House and One Bedroom Cottage. * * * * See end of this description for i ...
From $906 per night (USD)
VRBO
From $454 per night (USD)
VRBO
Waterfront Chatham Retreat w/ WiFi & Privacy
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
1 Bedroom- 1 Bath- Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of ...
From $454 per night (USD)
VRBO
From $462 per night (USD)
VRBO
Idyllic Cape House Close to Beaches
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Idyllic cape house close to beaches and ponds, as well as walking distance to restaurants, bars, ice cream, and shops in ...
From $462 per night (USD)
VRBO
From $1128 per night (USD)
VRBO
Chatham's Best Views-Harbor & Atlantic; On the Beach 4 Kayaks, 2 SUP's, 5 chairs
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
This exquisite ONE (1) family home, “Upside Down” house, easily compares favorably to ocean front suites at the Chatham ...
From $1128 per night (USD)
VRBO
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VRBO
TWO BEDROOM PET FRIENDLY COTTAGE -- 1/4 MILE TO RIDGEVALE BEACH
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
For those that love the Beach! Just 1/4 mile to beautiful Ridgevale Beach. Cape Cod cottage with two bedrooms and one ...
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VRBO
From $1046 per night (USD)
VRBO
Ocean views, path to beach, short walk to lighthouse and town, sleeps 12
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
This listing combines a large house having a deck with a beautiful view of the ocean and an adjacent cottage allowing fo ...
From $1046 per night (USD)
VRBO
From $1371 per night (USD)
VRBO
Perfect House to Enjoy Family & Friends!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Main house has 3 bedrooms 2 baths. Open floor plan is great for a big group. Apartment has a full kitchen, living area a ...
From $1371 per night (USD)
VRBO
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VRBO
Sea Mist Cottage by the sea w/ central AC & views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3 Bedroom - 2 Baths - Sleeps 6 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
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VRBO
From $566 per night (USD)
Expedia
Your Perfect South Chatham Summer Stay!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
3 Bedrooms- 2 Bathrooms- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
From $566 per night (USD)
Expedia
From $6125 per night (USD)
VRBO
Sweeping Ocean Views, Gorgeous Home With Guest Cottage, Pool and Tennis Court
Bedrooms:
5
Bathrooms:
7
Sleeps:
16
This cherished family home + guest cottage in coveted section of North Chatham is available for only one or two weeks e ...
From $6125 per night (USD)
VRBO
From $841 per night (USD)
VRBO
Ocean & Marina Views From This Charming Cottage! Walk To Beach & Town.
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Charming cottage right next to Outermost Marina with views of the boats & water. The quintessential beach house! If you ...
From $841 per night (USD)
VRBO
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VRBO
SHORT WALK TO LIGHTHOUSE BEACH AND TOWN....WATERFRONT ON MILLPOND WITH PATH TO WATER!!
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
Fabulous Old Village Location, Minutes to Lighthouse Beach and Town * * * * See end of this description for inf ...
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VRBO
From $412 per night (USD)
VRBO
SHORT WALK TO LIGHTHOUSE BEACH, ANDREW HARDINGS LANE BEACH AND TOWN!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Close to Town, Lighthouse Beach and Andrew Hardings Lane -- Desirable Old Village Location! * * * * See end of ...
From $412 per night (USD)
VRBO
From $551 per night (USD)
VRBO
Peaceful, Charming, Quiet, Airy, Cozy - Take A Look!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This 3 bedroom 2 bathroom two-story cape is private, quiet, and overlooks a lovely cranberry bog. Inside it's airy and o ...
From $551 per night (USD)
VRBO
From $2418 per night (USD)
VRBO
Amazing Location Chatham / walk to Town Beaches and CBI
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
This exquisitely furnished, charming Cape Cod house is within an easy walk of Chatham's beaches, Fish Pier, Lighthouse, ...
From $2418 per night (USD)
VRBO
From $650 per night (USD)
VRBO
AC, Pool, Hot Tub, Fenced Yard, Beach vacation home
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Spacious four bedroom, two bathroom, single family home with central air, above ground pool, hot tub, fire pit, and fenc ...
From $650 per night (USD)
VRBO
From $1661 per night (USD)
Expedia
Sail Loft: 489-C Updated Chatham Family Compound, Heated Pool w/Hot Tub, Walk to Town/Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This property is professionally managed by Pretty Picky Properties Updated Chatham Family Compound, Heated Pool with Ho ...
From $1661 per night (USD)
Expedia
From $598 per night (USD)
VRBO
Summer Hydrangea: Chatham's Truly Exceptional Summer Retreat
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to Summer Hydrangea, quite possibly the finest property value for an exceptional summer rental in Chatham. Priva ...
From $598 per night (USD)
VRBO
From $471 per night (USD)
VRBO
Pondfront cottage on Stillwater Pond
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Set your clocks back 80 years, and fish for your breakfast from your own dock or row-boat. This setting has been descri ...
From $471 per night (USD)
VRBO
From $445 per night (USD)
VRBO
S Chatham Ma 02659 Seasonal Cottage, Walk to Pleasant Street Beach DOG FRIENDLY
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Cottage has been in family for over 50years but updated over the years. Seasonal beach cottage 1 full bath, king bedroo ...
From $445 per night (USD)
VRBO
From $2436 per night (USD)
Expedia
Sand Simeon - Relax, Unwind, Repeat!!
Bedrooms:
6
Bathrooms:
6
Sleeps:
14
6 bedrooms- 6.5 Bathrooms- Sleeps 14 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. ...
From $2436 per night (USD)
Expedia
From $639 per night (USD)
VRBO
Sea views steps to Ridgevale Beach - Airy Cottage. Modern Amenities. Pet.linen
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Pet ok with approval first. Bright and airy cottage sleeps max 5 (2 BR - 1Q, 2T) plus single pull out sofa bed in hi liv ...
From $639 per night (USD)
VRBO
From $653 per night (USD)
VRBO
Chatham Lakefront home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Just 1.5 miles to Main Street Chatham, AC and newly finished basement The Space: This home is represented ...
From $653 per night (USD)
VRBO
From $1134 per night (USD)
VRBO
North Chatham Waterfront Oasis
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Amazing views! Enjoy the views of Pleasant Bay out to the ocean and the Outer Beach! This 4 bedroom 3 bath home is spaci ...
From $1134 per night (USD)
VRBO
From $493 per night (USD)
VRBO
Walk to Ridgevale Beach in 7 minutes, Central Air, Beautiful yard Fast Internet
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Adorable Chatham Ridgevale Beach House With Beautiful Gardens! *******7 night minimum stay Saturday to Saturday***** ...
From $493 per night (USD)
VRBO
From $2136 per night (USD)
VRBO
Historic Sea Captain's Home in Downtown Chatham
Bedrooms:
5
Bathrooms:
8
Sleeps:
18
8 Bedrooms- 5.5 Bathrooms- Sleeps 18 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. ...
From $2136 per night (USD)
VRBO
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Expedia
Sea Glass Cottage Near Nantucket Sound Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
3 bedroom- 2 bath- sleeps 7 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of ...
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Expedia
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VRBO
Walk to Beach Central AC WiFi Beach Pearl
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
2 bedrooms- 2 baths- sleeps 5 During peak summer weeks, our properties typically require a 7-night stay, either Friday-F ...
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VRBO
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Expedia
Family Chatham Retreat—Deck, Kayak & Outdoor Fun
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
3 Bedroom-3 Bathroom- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
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Expedia
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VRBO
Quiet North Chatham Getaway with Scenic Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
1 Bedroom- 1 Bathroom- Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
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VRBO
From $797 per night (USD)
Expedia
Lake front, Near Beach, AC, WiFi, Pet Friendly near Bike Path
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
3 Bedroom - 2.5 Baths - Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $797 per night (USD)
Expedia
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VRBO
Chatham Ranch Retreat Near Hardings Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3 Bedroom - 2 Baths - Sleeps 6 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
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VRBO
From $1054 per night (USD)
Expedia
The Heron's Nest - Sea Breezes & Sweet Dreams
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
4 Bedroom- 3 Bathroom- Sleeps 9 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $1054 per night (USD)
Expedia
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VRBO
Seaside Serenity Awaits at The Cape House!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
3 Bedrooms- 2 Bathrooms- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
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VRBO
From $784 per night (USD)
Expedia
Beachside Bliss: Dog Friendly & Breezy Stay
Bedrooms:
2
Bathrooms:
1
Sleeps:
8
3 Bedroom - 2.5 Baths - Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $784 per night (USD)
Expedia
From $1819 per night (USD)
VRBO
Walk to Beach and Town, Hot tub, Sleeps 8, Pet Friendly
Bedrooms:
5
Bathrooms:
3
Sleeps:
8
3 Bedroom (2 Primary) - Loft - 5.5 Bathroom - Sleeps 8 During Peak Summer Season Until Labor Day - a 7-night Friday-to-F ...
From $1819 per night (USD)
VRBO
From $670 per night (USD)
Expedia
Ocean views Walk to Beach Pet Friendly AC Private
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
4 Bedroom - 4 Baths - Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. This ...
From $670 per night (USD)
Expedia
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VRBO
Captain's Row: Pool, Tennis & Chatham Charm
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
2 Bedroom - 3 Bathroom - Accommodates 6 Comfortably During peak summer weeks it is typical for our properties to require ...
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VRBO
From $579 per night (USD)
Expedia
The Cape Escape: Walk to Harding's Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
4 Bedroom- 2 Bathroom- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $579 per night (USD)
Expedia
From $793 per night (USD)
VRBO
3 bed 3 bath. Premium linens provided. Pet friendly
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
When you arrive you will find that our architect maximized light, air and views, with great flow from the upstairs vault ...
From $793 per night (USD)
VRBO
From $1283 per night (USD)
VRBO
Walk to the Beach ~ Chatham rental
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
WALK TO JACKKNIFE COVE BEACH in Chatham from this charming, clean, and well-kept home. Enjoy s'mores with the kids at ou ...
From $1283 per night (USD)
VRBO
From $1656 per night (USD)
VRBO
LOCATION, LOCATION 200 YDS TO CHATHAM VILLAGE & BEACH WITH GREAT WATER VIEWS
Bedrooms:
3
Bathrooms:
5
Sleeps:
13
Location ! Location! Location ! Everything within walking distance . . . 200 yards to Chatham downtown, 200 yards to pub ...
From $1656 per night (USD)
VRBO
From $1059 per night (USD)
VRBO
Charming , very private 4 bedroom, 3.5 Bath Cape. Walk to Town & Oyster Pond
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
A charming 4 bedroom, 3.5 bath cape with large kitchen and private backyard, patio and deck that abuts conservation land ...
From $1059 per night (USD)
VRBO
From $821 per night (USD)
VRBO
Location, location, location
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Brand new remodeled kitchen. Charming 4 bedroom cape. Great location! Not your typical rental. We only rent a few we ...
From $821 per night (USD)
VRBO
From $2131 per night (USD)
VRBO
Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!
Bedrooms:
10
Bathrooms:
9
Sleeps:
21
This wonderfully renovated 1877 home, winner of the 2025 Building & Remodeling Industry of Cape Code Best Rennovation aw ...
From $2131 per night (USD)
VRBO
From $3195 per night (USD)
VRBO
Chatham Estate. Heated Pool, Sleeps 16+, AC, walk to beach! 1.3 mi from town.
Bedrooms:
5
Bathrooms:
8
Sleeps:
18
New heated gunite pool. 18X40 with automatic pool cover, and completely fenced in for safety. Design includes many plant ...
From $3195 per night (USD)
VRBO
From $313 per night (USD)
VRBO
Walk to School House Pond in Chatham.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This 2500sq ft house is 8yrs old and offers all the toys including a hot tub, sauna, bikes and kayaks for guest use. Fro ...
From $313 per night (USD)
VRBO
From $428 per night (USD)
VRBO
Fully Renovated Chatham 3 Bedroom with Water Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Dog friendly, patio and fire pit, walk to Stage Harbor and Lighthouse Beach The Space: This home is repres ...
From $428 per night (USD)
VRBO
From $532 per night (USD)
VRBO
Charming Cape Cottage in Chatham, 2 Min From Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Forest Sands cottage is comfortably decorated in Classic Cape style, a 2 minute walk from Forest Beach, and 10 minute sp ...
From $532 per night (USD)
VRBO
From $461 per night (USD)
VRBO
Spacious, private cottage just a few minutes walk to Ridgevale Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summer living less than a 1/2 mile from one of Cape Cod's best beaches! This home offers room to spread out, with living ...
From $461 per night (USD)
VRBO
From $480 per night (USD)
VRBO
Secluded Chatham Cottage Near Hardings Beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to our totally updated 'old Cape' style cottage. Guests have access to a wide variety of indoor, outdoor, and b ...
From $480 per night (USD)
VRBO
From $611 per night (USD)
VRBO
Beautiful home near Jacknife Beach and bike trail
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
This newly renovated home has 3 bedrooms and 2 1/2 baths,and is located in a nice quiet neighborhood. This home is centr ...
From $611 per night (USD)
VRBO
From $794 per night (USD)
VRBO
Outermost Waterfront Chatham Home w/ Wraparound Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Right down the hill from the famous Chatham Light House, this one-floor living, 2 bedroom, 2 full bath end unit with wr ...
From $794 per night (USD)
VRBO
From $458 per night (USD)
VRBO
Charming Air Conditioned Chatham Vacation Home Walk to Beach & Tennis
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This charming house is located on a landscaped, level lot on a quiet, dead end lane just 4/10 mile from Forest Beach on ...
From $458 per night (USD)
VRBO
From $419 per night (USD)
VRBO
Carriage House with Beautiful Water View, Steps to Beach & Main Street
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located overlooking Chatham's beautiful Oyster Pond, this two bedroom carriage house is the perfect location for your Ca ...
From $419 per night (USD)
VRBO
From $290 per night (USD)
VRBO
THREE BEDROOM UPDATED HOME--CLOSE TO FISH PIER AND TOWN.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Cute Chatham Getaway - Just 6/10's of a Mile to Chatham Fish Pier and 8/10's of a mile into Town center. * * * * ...
From $290 per night (USD)
VRBO
From $300 per night (USD)
VRBO
Stay in a Chatham Windmill! Beautiful Water View, Steps to Beach & Main Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
NEWLY RENOVATED CHATHAM WINDMILL for your special Cape Cod vacation experience! Located overlooking Chatham's beautiful ...
From $300 per night (USD)
VRBO
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VRBO
300 Yds on Sidewalk to Hardings Beach; On Private 1.5 Acres.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
If you have children or grandchildren, Blue Skye is for you. Lots of lawn to run and play, but they are far from the st ...
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VRBO
From $357 per night (USD)
VRBO
Cozy renovated classic Cape cottage a short walk to Forest Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This cute 2 bedroom 1 bath cottage was recently completely renovated inside and is bright, clean and cozy. It is locat ...
From $357 per night (USD)
VRBO
From $2873 per night (USD)
VRBO
Exquisite Old Cape Charm, Spectacular Views, Huge Private Beach, Sleeps 20
Bedrooms:
6
Bathrooms:
13
Sleeps:
20
This is the old Cape Cod at its loveliest and most peaceful. Although the oldest part of the house was originally a cott ...
From $2873 per night (USD)
VRBO
From $308 per night (USD)
Expedia
Cape Cod Chatham Water View Retreat
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Secluded Cape Cod Chatham retreat on tidal estuary creek. Conservation land assures privacy. Easy and safe private entra ...
From $308 per night (USD)
Expedia
From $332 per night (USD)
VRBO
Chatham Cottage on the Big Pond One Mile to Ocean Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Get away and relax at our cottage on White Pond in beautiful Chatham Cape Cod. The cottage has a private fresh water bea ...
From $332 per night (USD)
VRBO
From $362 per night (USD)
VRBO
Near Harding's Beach, 4 min walk to Oyster River. 3BR, 2Bath, enclosed deck area
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Just off of Barnhill Rd on the way to popular Harding's Beach, this air conditioned, updated three bedroom house off ...
From $362 per night (USD)
VRBO
From $634 per night (USD)
VRBO
Location Location! Perfect 2-Bedroom Condo On Main Street In Chatham
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Pet Friendly! Two bedroom luxury vacation condo on second floor of home in the heart of Chatham Village! Head up the sta ...
From $634 per night (USD)
VRBO
From $1503 per night (USD)
VRBO
SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to the SeaGlass House! Charming and bright, open concept Cape house perfect for creating long lasting memories. ...
From $1503 per night (USD)
VRBO
From $2135 per night (USD)
VRBO
Beachfront Nantucket style home with amazing views on 3 acre estate setting
Bedrooms:
1
Bathrooms:
5
Sleeps:
9
'The Bluff House' is a very private turn of the century informal home located down a private country lane directly on th ...
From $2135 per night (USD)
VRBO
From $404 per night (USD)
Expedia
Chatham Home Near the Bike Trail & Nantucket Sound (1524)
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover the perfect blend of style and convenience in this lovely, contemporary Chatham home, ideal for up to six guest ...
From $404 per night (USD)
Expedia
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VRBO
Beautifully Maintained 3BR Colonial Close to Forest Beach (1577)
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience classic Cape Cod charm in this thoughtfully maintained three-bedroom, two-bath colonial, ideally located just ...
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VRBO
From $830 per night (USD)
VRBO
Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach! A/C
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Spend your Chatham vacation at the POOL! This wonderful home is just minutes to everything downtown Chatham has to offer ...
From $830 per night (USD)
VRBO
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VRBO
Pet friendly home with central air (1998)
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Tucked away on a quiet residential dead-end road, this charming and dog-friendly Cape-style home offers a relaxing retre ...
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VRBO
From $458 per night (USD)
VRBO
Old Cape Cod Charm Chatham Beach House; Walk to Hardings Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
You will love Rhododendron House -- a recently updated 2 bedroom vacation house. This private hilltop retreat is located ...
From $458 per night (USD)
VRBO
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VRBO
Delightful Cottage for Two
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This true Cape Cod cottage is ideal for a couple. Located in a 6 acre private community on beautiful White Pond. It is n ...
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VRBO
From $1147 per night (USD)
Expedia
5 Bed/2 Bath Sleeps 11. Walk to restaurants, town and more...
Bedrooms:
2
Bathrooms:
5
Sleeps:
11
Located just 1 mile from the fish pier and CBI, and 1.5 miles to downtown, we are close to all the best Chatham has to o ...
From $1147 per night (USD)
Expedia
From $334 per night (USD)
VRBO
Coastal Charm in South Chatham – Walk to Beach & Bike Trail!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Charming South Chatham Cottage - Walk to Beach & Bike Trail Escape to this peaceful South Chatham cottage, perfectly sit ...
From $334 per night (USD)
VRBO
From $1627 per night (USD)
Expedia
Stones Throw: 052-CS Alluring Chatham in-town home with pool, walk to it all
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This property is professionally managed by Pretty Picky Properties Alluring Chatham in-town home with pool, walk to it ...
From $1627 per night (USD)
Expedia
$\Cape Escape\ Sunny Renovated House - Walk To Beach, Pickleball, Central AC$
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VRBO
\"Cape Escape\" Sunny Renovated House - Walk To Beach, Pickleball, Central AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Walking Distance to the beach! Updated home with indoor/outdoor living and separate living room and family room both wit ...
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VRBO
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VRBO
Sea Captain's House - Beautiful Water View, Steps to Beach & Main Street
Bedrooms:
5
Bathrooms:
5
Sleeps:
9
Located overlooking Chatham's beautiful Oyster Pond, this home is the perfect location for your vacation. Take advantage ...
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VRBO
From $667 per night (USD)
VRBO
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This charming and totally renovated (see updated pictures below) Chatham home is on a private road in a downtown neighbo ...
From $667 per night (USD)
VRBO
From $609 per night (USD)
VRBO
In Town Newly Renovated Cape
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Location, Location, Location – New to the rental market, this fully renovated centrally located cape home checks all the ...
From $609 per night (USD)
VRBO
From $632 per night (USD)
VRBO
STYLISH CHATHAM HOUSE
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Located within walking distance to a small beach and quick drive to the local shops and restaurants of Main Street i ...
From $632 per night (USD)
VRBO
From $1223 per night (USD)
VRBO
Cozy Family Home in Chatham - Firepit, Game Room, Large Deck, Yard + More
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This lovely home is the perfect getaway for families or a group of friends looking for a home filled with entertainment ...
From $1223 per night (USD)
VRBO
From $458 per night (USD)
VRBO
Quaint Two Bedroom Lakeside Cottage #18 with Screened-in Porch in Chatham
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Must bring your own linens. New kitchen, granite counter tops, new hardwood floors, new drywall and paint. Cathedral c ...
From $458 per night (USD)
VRBO
From $933 per night (USD)
VRBO
Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond in the heart of Chatham, Cape Cod, Massachus ...
From $933 per night (USD)
VRBO
From $599 per night (USD)
VRBO
Ocean-Front Condo Sleeps 6 (Light-filled end unit facing Ocean on Starfish Ln)!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Right down the hill from the famous Chatham Light House, this one-floor living, 2 bedroom, 2 full bath end-unit condo is ...
From $599 per night (USD)
VRBO
From $1752 per night (USD)
Expedia
Vacation in the heart of Chatham and walk to everything. Oyster Pond Beach is right around the corner!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Experience downtown Chatham! No need to drive when you can walk to everything. This charming rental features a classic f ...
From $1752 per night (USD)
Expedia
From $587 per night (USD)
VRBO
Marshside Escape: Walk to Cockle Cove
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
3 Bedroom - 3.5 Baths - Sleeps 6 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $587 per night (USD)
VRBO
From $387 per night (USD)
Expedia
Steps to Private Association Beach. End Unit Condo at Outermost Harbor.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Updated Condo at Outermost Harbor. Enjoy amazing views of the famous Chatham sandbars or catch a glimpse of playful seal ...
From $387 per night (USD)
Expedia

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